The BOSS PLAN is our premier service offering designed to help an organization quickly and effectively identify, diagnose and implement changes that will lead to an increase in sales, profitability and a decrease in the sales cycle timeline using the proven methods outlined in the book, “The Sales Boss: The Real Secret to Hiring, Training and Managing a Sales Team.”

 This overview is intended to give insight into a typical engagement between The Sales Boss and client organizations.


Timeline: Typically four-six weeks

Average fee: $10,000 - $75,000

Time & Fee Variables:

The size of the company, the complexity of sale, availability of data, composition of the team are the final determiners.  

During this phase, the Sales Boss team does a deep analysis of every aspect of the sales organization to understand what is the current state of sales and to identify which items can be optimized to produce the fastest results. Our full report will include detailed examples and suggestions of critical optimizations and the “how” and “when” these should be optimized as well as benchmarks to target for outcomes.

Jonathan Whistman, the SALES BOSS, will work directly with you and your key staff closely to get the most out of every session.

Jonathan Whistman, the SALES BOSS, will work directly with you and your key staff closely to get the most out of every session.

The deep-dive includes:


 A full evaluation of the sales team including sales leadership.  The evaluation is done through a variety of methods including:

Online Psychometric Assesment: The PXT assessment allows for a scientific understanding of the “DNA” of the current team and why some are more successful than others and serves as a template for creating a hiring profile for future hires.  This also serves to inform how likely the current team will be able to execute any future plan or respond to caching and learning opportunities.

Online DiSC Assesment: This online assessment allows for an understanding of the behavioral traits associated with each member of the team and gives insight into how they are likely to interact with customers, managers, and the structures that are in place.  These   for crafting metrics and training, and coaching programs that will yield more substantial and immediate impact.

Personal Interviews: Personal interviews with each team member are conducted in person or through video conference to help gain insights into them as a salesperson or sales leader, their customers, the company history, processes, etc.

Observation:  Each team member’s approach is analyzed using the most appropriate and available method possible. Typically this includes, reviewing recorded phone calls, sitting in as an observer on live calls, team meetings, and other opportunities.  In addition, reviewing each critical stage of their selling process (or leadership).  For instance, emails and written communication, proposals and other personalized sales collaterals.


A key deliverable of this portion is an ideal hiring profile and a coaching/development plan for each team member and suggestions on fit (or no fit) for current and future roles. We’ll also help outline what metrics should be utilized when onboarding new team members and what realistic targets should be.

Everything he said he would bring to our company he did. He was efficient and executed at the highest level. His understanding of sales is as a true master who inspires the sales team to hit goals they never dreamed possible.
— G. McCracken, MD


We assess the revenue engine from top to bottom.  This portion is dedicated to gaining a complete understanding of how a prospect discovers the company and the process that a lead takes to close.

MQL, SQL, Sales Stages, current conversion rates, quote process, and closing. During this review, we will identify what causes leads to leak out of the system, or get stuck. We will also identify how to prevent pipeline bloat and which key metrics are leading and lagging indicators so that a plan can be developed to increase retention and speed through the pipeline. You will find this gives renewed confidence to forecasting.  Compensation and incentives are evaluated for impact, non-intended outcomes and effectiveness.


Every sales organization uses technology to enable the sales process.  Our systems review will help identify what is needed to improve the customer experience, speed to close, and the tools for effectively managing the team and planning for growth.  The technology review will include the current state, but also concrete suggestions on optimization and current trends leading organizations are utilizing.


Key to any final sales plan is understanding the market.  We rely upon deep sales experience across a wide variety of industries, however, we take the time to understand your customer and your product so that we can be confident that any changes in the sales approach and targeting are successful.  In addition, while we don’t believe in imitating your competition- we also evaluate their approaches to the market and when available we secure benchmarks that can be used as a source of validation.


This stage of the Boss Plan is complete when robust findings and an action plan is shared with you and you are clear on what actions can be taken to experience short-term immediate successes and also to sustain growth through the implementation of the plan.


PLanning sales.jpg

Phase 02: Getting It Done

Phase Two is where we implement any plan of action.  Typically by this phase, our clients are already implementing some of the early insights gleaned as phase one progressed.  It is now that the pace of change picks up dramatically.  This phase is a monthly plan with an all-inclusive fee attached to outcomes.  We don’t tie you into long-term agreements as we only desire you to continue utilizing our help as you are actively seeing the benefits.

Timeline: month-to-month with an estimated minimum & maximum timeframe established.

Average fee:  $3750 mo - $42,000 mo

Fee Variable:  The size of the monthly fee is determined by the scale of the changes & pace desired by the client.

*Senior Leadership positions hired under our recruitment plan*

While this phase is dynamic and customized for each client some typical deliverables are:

  • Building the team hire/ replace as needed

  • Training & development

  • Scrip & sales process execution/ implementation

  • Technology improvements

  • Compensation plans adjusted

  • Collateral development